Hydrochloric Acid → HCID 19763703, compound

HRID 248430Notes

Reaction equation

HRID 248430 reaction equation
[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6]1.[BH4-].[Na+].Cl>CO>[CH3:1][N:2]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:12])[CH2:4][N:5]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 19763671HCID 19763671, compound

Product 1

HCID 19763703HCID 19763703, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-methyl-N-phenethyl-2-[3-formylpyrrol-1-yl]acetamide in methanol, stirred in an ice bath, is added in portions 5 molar equivalents of sodium borohydride. The mixture is stirred in the cooling bath for an additional 45 minutes and 1N aqueous HCl solution is added dropwise until the pH of the mixture is approximately 6-7. The resulting mixture is concentration in vacuo and the residue obtained is partitioned between ethyl acetate and water. The organic layer is dried over MgSO4 and concentrated in vacuo to give N-methyl-N-phenethyl-2-[3-hydroxymethylpyrrol-1-yl]acetamide. This material is used without further purification in the next step.

Workup

  1. concentrationconcentration in vacuo
  2. customthe residue obtained
  3. customis partitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39a63d29f5894f778071bfd21b9b6358
Source dataset
uspto-grants-1993_05
Patent number
US05210208

Reaction notes

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